5 Things I’ve Learned About Leadership Working With A New Assistant

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If you’re like most leaders, you’re almost always adding someone new to your team, whether that’s a new volunteer, a new board member or a new staff member.

In a growing organization, a changing team is an organizational constant.

I had this experience recently. As some of you may know, I recently transitioned to working with a new assistant after 7 (great) years with my former assistant.

Few people impact you more directly than an assistant. That’s why I knew finding a replacement for Sarah Piercy would be a tough challenge. (Sarah and I talk about what made our working relationship amazing in this interview.)

When I found out Sarah would be heading out on maternity leave, I immediately turned to eaHELP, and I’m so glad I did.

I knew eaHELP provides virtual assistant services based in the U.S. They immediately matched me with a highly competent and smart new assistant, also named Sara.

What I didn’t realize is how in-depth eaHELP’s infrastructure and system is designed to support both me and Sara throughout the process. That has proven to be such a bonus as we’ve navigated the first 90 days.

Their help and expertise have been invaluable.

But even with all the support in the world, there are new things to learn and new adjustments to make.

Here are 5 things I’ve learned about leadership (and especially about myself) working with my new EA.

1. You have to let go of the past to embrace the future

Sometimes you’re really glad to see a team member go. Other times, you’re actually really sad to see the team member step away. The second scenario describes how I felt about losing Sarah Piercy, even for a year.

Even though I was really happy that Sarah and her husband were going to become parents for the first time, I felt a pretty deep sense of loss. Sarah and I had worked together for 7 years and she was fantastic at what she did. Plus, we had a ton of fun working together.

I realize as much as I prepared myself for Sarah’s departure, I actually felt the loss more after she left than before.

That’s natural, but I had to be very careful not to project that on my new assistant (or others).

I actually felt quite a bit of internal resistance to all the changes that were taking place during the first month or two. (The irony was not lost on me since I wrote a book about overcoming opposition to organizational change.)

But I soon saw that not letting go of the past is the first, sad step toward living in the past. And I’ve seen so many leaders do that, to everyone’s detriment.

If you want to embrace the future, you’ve got to let go of the past, no matter how much you may have enjoyed it.

And ironically, once you do, you’ll see how awesome the present is and how good the future can be.

If you want to embrace the future, you've got to let go of the past. Click To Tweet

2. Ambiguity is a terrible training manual

One key to an easy transition is to have your systems and methodology written down.

I’ve done a decent job of writing down the mission, vision, strategy and culture of Connexus Church, where I serve.  (I outline how I did that here.)

My new assistant Sara’s main job is not to help me with the church side of my life, but with this blog, with my leadership podcast, with my speaking engagements and the rest of my life. Those things have grown exponentially over the last few years, but I’d never made the time to write down the mission, vision, strategy or even culture I’m trying to embody in those areas.

That makes training someone new much more difficult. Ambiguity is a terrible training manual.

Ambiguity is a terrible training manual. Click To Tweet

This kind of ambiguity almost always results in a leader telling a new team member what’s wrong, not what’s right. The dialogue can almost end up sounding like this:

No, I don’t think that’s right.

Okay, well let me try it this way, is this better?

No, that’s not it either.

How about this?

Um…not really.

Well, can you help me understand what you’re shooting for?

I’m not 100% sure actually.

Fortunately for me, my new assistant Sara is sharp and we avoided countless rounds and rounds of this.

We actually found a groove on culture, communication and process faster than we might have largely because she is really good at reading between the lines and is highly motivated to get there fast.

But the process has taught me I need to codify as much as I can quickly.

You can’t scale ambiguity.

You can't scale ambiguity. Click To Tweet

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3. Reasonable expectations are your friend

Like many leaders, I am an optimist.

And so I regularly underestimate how much time things take, how many bumps there will be and I often assume everything that’s unreasonable is reasonable.

In many ways, that’s a strength, but it’s also far healthier to have reasonable expectations and timeframes in place.

Underestimating the challenges in front of you only creates new challenges.

There will be a transition period with any change. And as a leader, you need to make time for it.

If I was guilty of anything in the first 60 days, it was probably that I kept assuming the transition was ending, when in fact, it was perfectly normal to still be in transition.

Ironically, if you plan on a transition, the transition period will end sooner than if you pretend there’s no transition.

Underestimating the challenges in front of you actually creates a new challenge. Click To Tweet

4. Relationship managers are a GREAT idea

Usually, when you hire a new person, it’s 100% up to you and them to figure out how to make the relationship ideal.

eaHELP does something unique: they assign a Relationship Manager to assist both you and your assistant to work through all the dynamics of the transition.

The Relationship Manager’s job is to check in, help identify and find solutions for any bumps and challenges that come up as your working relationship develops, and make sure the leader and the assistant succeed. This has proved tremendously helpful to both Sara and me.

And this isn’t an elite package; everyone who uses eaHELP gets one. Brilliant.

I think if more companies and churches did this, you would see far greater success in both team member retention and satisfaction.

eaHELP founder Bryan Miles and I talk about what relationship managers do and cover the story of the rise of eaHELP in Episode 45 of my leadership podcast (an interview which happened long before I became a client. :))

5. Lead yourself, not just the new team member

It’s easy to assume that in a transition, you need to lead the new team member. That’s true. You do.

But it’s easy to forget that you also need to lead yourself.

When you’re in a transition, everything changes. This means you have to change. Your systems, expectations, and even the chemistry is going to be different.

One of the best ways to lead yourself is to set time aside to work on it, not just in it. Most of us run hard enough that there’s not a lot of extra time to think, reflect, and work on the system.

Change that and make the time.

You’ll be glad you did. So will your assistant.

The best leaders don't just lead others well; they lead themselves well. Click To Tweet

Need An Assistant?

I’ve always said I couldn’t do what I do without a fantastic assistant.

That has become even more apparent to me in the last few months. Man, am I thankful! I realize how valuable a great assistant is, and how helpful it is to be matched up with a highly competent person straight out of the gate.

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Carey Nieuwhof
Carey Nieuwhof

Carey Nieuwhof is a best-selling leadership author, speaker, podcaster, former attorney, and church planter. He hosts one of today’s most influential leadership podcasts, and his online content is accessed by leaders over 1.5 million times a month. He speaks to leaders around the world about leadership, change, and personal growth.